Ester of butyl alcohol



Patented Jan. 4, 1927.

UNITED STATES 1P TEN.1 Fm

ROBERT H. mm semen, .13., or 'nvansron, ILLINOIS..-

.nsrnn. or sum snconon.

No Drawing.

. My invention relates to a new composition of matter. 'It consists, of the esters of butyl alcohol with the higher fatty acids, elther singly or mixed. The usefulness of such a composition will be a parent trom certaindetails of the description of the'invention,

and also from my copielnding, application Serial No. 31,915, filed ay 21, 1925. For

example, I have found the butylesters of the higher fatty acids to be desirable ingredients of the film left by the evaporation of pyroxylin lacquers. Such esters make the film relatively pliable and soft, the; extent of increase in pliability and softness depending. upon- Eroportion of such ester added as a h the softe er. y

T butyl esters of organic acids have only recently acquired a new importance. Formerly, butyl alcohol, one of the essential materials of manufacture, was of theoreti-. cal interest almost exclusively. 'Ihe quantity available was small. The price was Stimulated by the increasing high. Now a very successful process of producing butyl alcohol b fermentation. has made this alcohol availa' le in tank-car lots. Indeed, the availability of butyl' alcohol and of its derivative, butyl'acetate, in adequate quantities, is responsible in large measure for 'the recent great expansion of the lacquer industry for finishing automobiles and furniture.

importance of butyl alcohol, I have invente anew composition of matter containing the hydrocarbon radical (C H,) of butyl alcohol, namely butyl esters of the 'higher fatty acids.

I may make tlie butyl esters of the higher -fatty acids by the reaction otbutyl alcoholon the acid whose esterit is desired to produce, in the presence of hydrogen chloride or-sulfuric acid. as the catalyst, the tempera- ..ture ef reaction and the time allowed for may 284 parts by weight-of stearic acid the suit factory conditions.

Togmake butyl stearate for example, I

with 74 parts of butyl. alcohol and;4 .parts I of concentrated sulfuric acid. .The mixture 'is-then boiled gently ina'pct provided with a-'refl condenser for return ng vapors of uncombinedbutyl alcohol. After six hours,

" sufiicient. precipitated calcium. carbonate (whiting v furic'aci and the pot is disconnected from.

is added to neutralize the S111- the reflux condenser-and'connected, instead, with a down condenser so that the vapors acidsof the alip combination to occur being adjusted to.

droxy acids.

Application filed August 21, 1925. Serial No. 51,685.

of butyl alcohol, as they condense, run

down into-a receiver.; When. no more material distils butyl stearate itself is distilled in a. vacuum 8f the degree produced by an efiicientvacat temperatures below 190" the .uum pumpof thefoil-sealed type, by a pump commonly spoken of as an oil vacuum pump.

The high boiling point which nec essitates that the distillation be performedin vacuo indicates one of the merits of my new compositipns of matter, non-volatility at ordinary temperatures The but-yl esters resemble, to a degree, the glycerides of fats and certain oils. But the former are preferable for. certain uses. They are more soluble in certain organic solvents.- They are (almost colorless, after vacuum distillation, and they are not so unpleasant in'odor as lard, cotton-' seed oil, or castor oil.

The butyl estersinvented by me difi'er 1 I from the' corresponding ethyl estersespe- 'cially in volatility, somewhat as butyl alcohol differs from ethyl alcohol, with its relatively low boiling point.

My invention is not limited to the specific illustration iven; It includes esters of normal but 1 a cohol, with one or more. of the higher atty acids. Amongitho'se' acids may .Arachidic c n coon in t e specifications and claims, I meannot only the acids listed above, with their isomers and homologls, but also other saturated as the monocarboxylic dicarboxylic, or byhe words higher fatty'acids as used atic series containing more than 8 carbon atoms to the molecule, such' The esters} oi butyl alcohol" with these higher fatty acids are waxes or liquids, practically non-volatile at ordinary temperatures, and soluble. in alcohol, acetone," ether, and ethyl acetate. 'Butylstearate, as-made from normal butyl alcohol and commercial stearic" acid, is a colorless liquid at temperatures above18fC.; below 18 C., it freezes to a.

white. opaque wax. It is practically odor .less, insoluble in water, and unaifected by long exposure to air. Such propertiesmake these esters preferable to already known products, such as castor oil, for certain purposes.

Any one of my new esters is identified by saponification number, iodine absorption number, and melting point of the fatty acid derived from it by saponification and acidiligat on in the well known manner.

I do not. limit myself to any method of manufacture of the butyl esters or to any use or uses of them.

What I claim is 2- 1. A new composition of matter comprising a normal butyl ester of a higher fatty acid, saturated with respect to hydrogen.

2. A new composition of matter comprising a normal butyl ester of a fatty monocarboxylic acid containing more than eight carbon atoms to the. molecule, and saturated with respect to hydrogen.

3. A DOWtOlllpObltlOll of matter comprising lmtyl steai ate.

In testimony, that I claim the foregoing as my own I have hereto afiixcd my signa ture.

R. H. VAN SCHAACK, JR. 

